CN101402650B - Organotin coordination compound, preparation and uses thereof - Google Patents
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 30
- 238000002360 preparation method Methods 0.000 title claims abstract description 13
- 208000005718 Stomach Neoplasms Diseases 0.000 claims abstract description 6
- 206010017758 gastric cancer Diseases 0.000 claims abstract description 6
- 208000032839 leukemia Diseases 0.000 claims abstract description 6
- 201000007270 liver cancer Diseases 0.000 claims abstract description 6
- 208000014018 liver neoplasm Diseases 0.000 claims abstract description 6
- 201000011549 stomach cancer Diseases 0.000 claims abstract description 6
- 206010061306 Nasopharyngeal cancer Diseases 0.000 claims abstract description 5
- 229940079593 drug Drugs 0.000 claims abstract description 5
- 239000003814 drug Substances 0.000 claims abstract description 5
- 208000001894 Nasopharyngeal Neoplasms Diseases 0.000 claims abstract description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract description 18
- 239000003208 petroleum Substances 0.000 abstract description 12
- 230000001093 anti-cancer Effects 0.000 abstract description 6
- 239000013078 crystal Substances 0.000 abstract description 6
- JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical compound CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 abstract description 6
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 abstract description 6
- 238000010992 reflux Methods 0.000 abstract description 6
- 239000007787 solid Substances 0.000 abstract description 6
- 238000003756 stirring Methods 0.000 abstract description 6
- 238000001953 recrystallisation Methods 0.000 abstract description 5
- 238000002390 rotary evaporation Methods 0.000 abstract description 5
- 210000004027 cell Anatomy 0.000 description 9
- 239000002246 antineoplastic agent Substances 0.000 description 6
- 229940041181 antineoplastic drug Drugs 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 238000011160 research Methods 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 229910020813 Sn-C Inorganic materials 0.000 description 3
- 229910018732 Sn—C Inorganic materials 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- DQLATGHUWYMOKM-UHFFFAOYSA-L cisplatin Chemical compound N[Pt](N)(Cl)Cl DQLATGHUWYMOKM-UHFFFAOYSA-L 0.000 description 3
- 229960004316 cisplatin Drugs 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 208000002454 Nasopharyngeal Carcinoma Diseases 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- VMGAPWLDMVPYIA-HIDZBRGKSA-N n'-amino-n-iminomethanimidamide Chemical compound N\N=C\N=N VMGAPWLDMVPYIA-HIDZBRGKSA-N 0.000 description 2
- 201000011216 nasopharynx carcinoma Diseases 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- IOOMXAQUNPWDLL-UHFFFAOYSA-N 2-[6-(diethylamino)-3-(diethyliminiumyl)-3h-xanthen-9-yl]-5-sulfobenzene-1-sulfonate Chemical compound C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S(O)(=O)=O)C=C1S([O-])(=O)=O IOOMXAQUNPWDLL-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 231100000002 MTT assay Toxicity 0.000 description 1
- 238000000134 MTT assay Methods 0.000 description 1
- XJLXINKUBYWONI-NNYOXOHSSA-O NADP(+) Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-NNYOXOHSSA-O 0.000 description 1
- 229910020923 Sn-O Inorganic materials 0.000 description 1
- 229910009053 Sn—O—Sn Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
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- 229920002521 macromolecule Polymers 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
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- 229910052697 platinum Inorganic materials 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 231100000338 sulforhodamine B assay Toxicity 0.000 description 1
- 238000003210 sulforhodamine B staining Methods 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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Abstract
本发明公开了一种有机锡配位化合物，结构式为：
Description
技术领域technical field
本发明涉及一种有机锡配位化合物，及其制备方法，以及该化合物在制备抗癌药物中的应用。The invention relates to an organotin coordination compound, a preparation method thereof, and an application of the compound in preparing anticancer drugs.
背景技术Background technique
有机锡化合物的研究最早可追溯到十九世纪四十年代，但有机锡化学的真正繁荣始于20世纪80年代，当时人们在对金属抗癌药物的研究和筛选过程中，发现一些二烃基锡化合物具有比顺铂更高的抗肿瘤活性(Crowe，A.J.；Smith，P.J.；Atassi.G.，Chem.Biol.Interact.，1980，32，171)。此后，随着人们对有机锡化合物的研究不断深入，有机锡化学的研究领域和应用范围也随之不断扩大。The research on organotin compounds can be traced back to the 1840s, but the real prosperity of organotin chemistry began in the 1980s, when people discovered some dihydrocarbyl tin compounds during the research and screening of metal anticancer drugs. The compound has higher antitumor activity than cisplatin (Crowe, A.J.; Smith, P.J.; Atassi.G., Chem. Biol. Interact., 1980, 32, 171). Since then, with the deepening of research on organotin compounds, the research field and application range of organotin chemistry have also been continuously expanded.
发明内容Contents of the invention
针对上述现有技术，本发明提供了一种新的有机锡配位化合物，并提供了该化合物的制备方法及其应用。Aiming at the above-mentioned prior art, the present invention provides a new organotin coordination compound, and provides a preparation method and application of the compound.
一种有机锡配位化合物，结构式如下：An organotin coordination compound, the structural formula is as follows:
其中，nBu表示正丁基。Among them, n Bu represents a n-butyl group.
一种有机锡配位化合物的制备方法：向烧瓶中加入1mmol的二丁基氧化锡、1～1.5mmol的2-喹啉甲酸、30～50ml的苯，在45～50℃的温度下，搅拌回流5～7小时，冷却到室温，旋转蒸发，得到白色固体；用乙醚-石油醚重结晶，得到无色透明晶体，即为有机锡配位化合物；其中，乙醚与石油醚的体积比为1：1～2：1。A preparation method of an organotin coordination compound: add 1 mmol of dibutyltin oxide, 1 to 1.5 mmol of 2-quinolinecarboxylic acid, and 30 to 50 ml of benzene into a flask, and stir at a temperature of 45 to 50°C Reflux for 5-7 hours, cool to room temperature, and rotate to evaporate to obtain a white solid; recrystallize with ether-petroleum ether to obtain colorless transparent crystals, which are organotin coordination compounds; wherein, the volume ratio of ether to petroleum ether is 1 :1～2:1.
反应式为：The reaction formula is:
所述有机锡配位化合物在制备治疗胃癌、鼻咽癌、人肝癌或白血病的药物中的应用。Application of the organotin coordination compound in the preparation of medicines for treating gastric cancer, nasopharyngeal cancer, human liver cancer or leukemia.
本发明的有机锡配位化合物分子式为C72H96N4O10Sn4；分子量为1652.29，具有较高的抗癌活性，可以其为原料制备治疗胃癌、鼻咽癌、人肝癌或白血病的药物。与目前普遍使用的铂类抗癌相比，本发明的有机锡配位化合物具有抗癌活性较高、脂溶性好、成本低、制备方法简单等特点，为开发抗癌药物提供了新途径。The molecular formula of the organotin coordination compound of the present invention is C 72 H 96 N 4 O 10 Sn 4 ; the molecular weight is 1652.29, and it has high anticancer activity. drug. Compared with platinum-based anti-cancer commonly used at present, the organotin coordination compound of the present invention has the characteristics of high anti-cancer activity, good fat solubility, low cost, simple preparation method, etc., and provides a new way for the development of anti-cancer drugs.
具体实施方式Detailed ways
下面结合实施例对本发明作进一步的说明：The present invention will be further described below in conjunction with embodiment:
实施例1：制备有机锡配位化合物：向烧瓶中加入1.0mmol的二丁基氧化锡、1.0mmol的2-喹啉甲酸、30ml的苯，在45℃的温度下，搅拌回流6小时，冷却到室温，旋转蒸发，得到白色固体；用乙醚-石油醚重结晶，得到无色透明晶体，即为有机锡配位化合物；其中，乙醚与石油醚的体积比为1：1。产率85％，熔点192～194℃。Example 1: Preparation of organotin coordination compounds: add 1.0 mmol of dibutyltin oxide, 1.0 mmol of 2-quinolinecarboxylic acid, and 30 ml of benzene into the flask, stir and reflux for 6 hours at a temperature of 45 ° C, and cool At room temperature, rotary evaporation gave a white solid; recrystallization with ether-petroleum ether gave colorless transparent crystals, which were organotin coordination compounds; wherein, the volume ratio of diethyl ether to petroleum ether was 1:1. The yield is 85%, and the melting point is 192-194°C.
经红外光谱分析和核磁共振分析，结果如下：Through infrared spectrum analysis and NMR analysis, the results are as follows:
红外光谱(KBr，cm-1)：vas(C＝O)1589，vs(C-O)1381，vas(Sn-C)588，vs(Sn-C)533，v(Sn-O)460，v(Sn-N)451，v(Sn-Cl)263，v(Sn-O-Sn)621。Infrared spectrum (KBr, cm -1 ): v as (C=O) 1589, v s (CO) 1381, v as (Sn-C) 588, v s (Sn-C) 533, v(Sn-O) 460, v(Sn-N)451, v(Sn-Cl)263, v(Sn-O-Sn)621.
1H核磁(CDCl3，ppm)：1H核磁(CDCl3，ppm)：δ8.85(d，1H，H-3)，8.32(d，1H，H-4)，8.26(d，1H，H-9)，8.11(d，1H，H-6)，7.80(dd，1H，H-8)，7.74(dd，1H，H-7)，0.88-1.81(m，12H，Sn-C4H9)。13C核磁(CDCl3，ppm)：δ172.3，156.9，145.5，133.7，139.1，132.4，129.6，127.6，126.1，(C9H6NO2)；22.8，31.7，45.3(-CH2-)，14.3(-CH3)；δ168.1(COO)。 1 H NMR (CDCl 3 , ppm): 1 H NMR (CDCl 3 , ppm): δ8.85 (d, 1H, H-3), 8.32 (d, 1H, H-4), 8.26 (d, 1H, H-9), 8.11(d, 1H, H-6), 7.80(dd, 1H, H-8), 7.74(dd, 1H, H-7), 0.88-1.81(m, 12H, Sn-C 4 H9 ). 13 C NMR (CDCl 3 , ppm): δ172.3, 156.9, 145.5, 133.7, 139.1, 132.4, 129.6, 127.6, 126.1, (C 9 H 6 NO 2 ); 22.8, 31.7, 45.3 (-CH 2 -) , 14.3 (-CH 3 ); δ 168.1 (COO).
元素分析：计算值C72H96N4O10Sn4：C，52.33；H，5.86；N，3.39；实测值：C，52.27；H，5.95；N，3.47％。 Elemental analysis: Calculated for C72H96N4O10Sn4 : C , 52.33; H , 5.86; N , 3.39; Found: C, 52.27; H, 5.95; N, 3.47%.
实施例2：制备有机锡配位化合物：向烧瓶中加入1.0mmol的二丁基氧化锡、1.5mmol的2-喹啉甲酸、50ml的苯，在45℃的温度下搅拌回流7小时，冷却到室温，旋转蒸发，得到白色固体；用乙醚-石油醚重结晶，得到无色透明晶体，即为有机锡配位化合物；其中，乙醚与石油醚的体积比为1：1。产率80％，熔点192～194℃。Example 2: Preparation of organotin coordination compounds: add 1.0mmol of dibutyltin oxide, 1.5mmol of 2-quinolinecarboxylic acid, and 50ml of benzene into the flask, stir and reflux for 7 hours at a temperature of 45°C, and cool to Rotary evaporation at room temperature gave a white solid; recrystallization with diethyl ether-petroleum ether gave colorless transparent crystals, which were organotin coordination compounds; wherein the volume ratio of diethyl ether to petroleum ether was 1:1. The yield is 80%, and the melting point is 192-194°C.
实施例3：制备有机锡配位化合物：向烧瓶中加入1.0mmol的二丁基氧化锡、1.0mmol的2-喹啉甲酸、50ml的苯，在50℃的温度下，搅拌回流6小时，冷却到室温，旋转蒸发，得到白色固体；用乙醚-石油醚重结晶，得到无色透明晶体，即为有机锡配位化合物；其中，乙醚与石油醚的体积比为2:1。产率82％，熔点192～194℃。Example 3: Preparation of organotin coordination compounds: add 1.0 mmol of dibutyltin oxide, 1.0 mmol of 2-quinolinecarboxylic acid, and 50 ml of benzene into the flask, stir and reflux for 6 hours at a temperature of 50 ° C, and cool After reaching room temperature, rotary evaporation gave a white solid; recrystallization with diethyl ether-petroleum ether gave colorless transparent crystals, which were organotin coordination compounds; wherein, the volume ratio of diethyl ether to petroleum ether was 2:1. The yield is 82%, and the melting point is 192-194°C.
实施例4：制备有机锡配位化合物：向烧瓶中加入1.0mmol的二丁基氧化锡、1.3mmol的2-喹啉甲酸、40ml的苯，在48℃的温度下，搅拌回流5小时，冷却到室温，旋转蒸发，得到白色固体；用乙醚-石油醚重结晶，得到无色透明晶体，即为有机锡配位化合物；其中，乙醚与石油醚的体积比为2:1。产率82％，熔点192～194℃。Example 4: Preparation of organotin coordination compounds: add 1.0mmol of dibutyltin oxide, 1.3mmol of 2-quinolinecarboxylic acid, and 40ml of benzene into the flask, stir and reflux for 5 hours at a temperature of 48°C, and cool After reaching room temperature, rotary evaporation gave a white solid; recrystallization with diethyl ether-petroleum ether gave colorless transparent crystals, which were organotin coordination compounds; wherein, the volume ratio of diethyl ether to petroleum ether was 2:1. The yield is 82%, and the melting point is 192-194°C.
试验例：本发明的有机锡配位化合物，其体外抗癌活性测定是通过MTT与SRB两种实验方法实现的，其原理为：Test example: the organotin coordination compound of the present invention, its in vitro anticancer activity measurement is realized by two kinds of experimental methods of MTT and SRB, and its principle is:
MTT分析法：以代谢还原3-(4，5-dimethylthiazol-2-yl)-2，5-diphenyl terrazolium bromide为基础，活细胞线粒体中存在与NADP相关的脱氢酶，可将黄色MTT还原成不溶性蓝紫色的Formazan，死细胞无此酶，MTT不被还原，用DMSO溶解Formazan后，可用酶标仪测定特征波长的光密度，进行有关数据处理，得出结论。MTT analysis method: Based on the metabolic reduction of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl terrazolium bromide, there is a dehydrogenase related to NADP in the mitochondria of living cells, which can reduce yellow MTT to Insoluble blue-purple Formazan, dead cells do not have this enzyme, and MTT is not reduced. After dissolving Formazan with DMSO, the optical density of the characteristic wavelength can be measured with a microplate reader, and the relevant data can be processed to draw a conclusion.
SRB分析法：Sulforhodamine B是一种粉红色蛋白质结合染料，可溶于水，可与生物大分子中的碱性氨基酸结合，其在515nm的OD读数与细胞数呈良好的线性关系，可定量计算出药物加量与有关细胞数目的数据。SRB analysis method: Sulforhodamine B is a pink protein-binding dye that is soluble in water and can be combined with basic amino acids in biological macromolecules. Its OD reading at 515nm has a good linear relationship with the number of cells and can be quantitatively calculated Data on drug dosage and related cell numbers were obtained.
以SRB分析法对人肝癌Bel-7402细胞株、人胃癌BGC-823细胞株、人鼻咽癌KB细胞株进行分析，以MTT分析法对人白血病HL-60细胞株进行分析，测定其IC50值，结果见表1，结论为：根据表中数据可知，本发明的抗癌药物，对人肝癌的抗癌活性较高，对于人胃癌、白血病的体外活性IC50值均大于顺铂的IC50值，可作为抗癌药物的候选化合物。The human liver cancer Bel-7402 cell line, the human gastric cancer BGC-823 cell line, and the human nasopharyngeal carcinoma KB cell line were analyzed by SRB assay, and the human leukemia HL-60 cell line was analyzed by MTT assay to determine the IC 50 The results are shown in Table 1, and the conclusion is: according to the data in the table, the anticancer drug of the present invention has higher anticancer activity to human liver cancer, and the in vitro activity IC values for human gastric cancer and leukemia are all greater than the IC of cisplatin 50 value, it can be used as a candidate compound for anticancer drugs.
表1有机锡配位化合物抗癌药物体外活性测试数据Table 1 In vitro activity test data of organotin complex compound anticancer drugs
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| Hongyun wang et al..Di- μ3-oxido-bis(μ2-quinaldato-κ2O:O)bis(quinaldato-κ2N,O)tetrakis[di-n-butyltin(IV)].《Acta Crystallographica Section E》.2007,第E64卷m197-m198以及supplementary materials. * |
| Hongyunwangetal..Di-μ3-oxido-bis(μ2-quinaldato-κ2O:O)bis(quinaldato-κ2N O)tetrakis[di-n-butyltin(IV)].《Acta Crystallographica Section E》.2007 |
| 尹汉东等.有机锡化合物二{氧合-二[杂环羧酸二丁基锡(IV)]}的合成、表征和二{氧合-二[2-噻吩甲酸二丁基锡(IV)]}的晶体结构.《有机化学》.2004,第24卷(第7期),770-774. * |
| 胡浩斌.有机锡配合物的抗癌活性研究进展.《陇东学院学报(自然科学版)》.2004,第14卷(第2期),48-53. * |
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